Triphenylphosphine → 3-Isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzoic acid methyl ester

HRID 883048Notes

Reaction equation

HRID 883048 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH:11]([CH3:13])[CH3:12])[CH:7]=[C:6]([OH:14])[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:35]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41]O)=[CH:36]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:5]=[C:6]([O:14][CH2:41][CH2:40][C:37]2[CH:38]=[CH:39][S:35][CH:36]=2)[CH:7]=[C:8]([O:10][CH:11]([CH3:13])[CH3:12])[CH:9]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 83731Thiophene-3-ethanolHCID 5363146Diisopropyl azodicarboxylateHCID 23072925Methyl 3-hydroxy-5-isopropoxybenzoate

Product 1

HCID 585289273-Isopropoxy-5-(2-thiophen-3-yl-ethoxy)-benzoic acid methyl esterYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-hydroxy-5-isopropoxy-benzoic acid methyl ester (71.4 mmol) in anhydrous THF (85 ml) is added under inert atmosphere successively triphenylphosphine (1.5 eq.) and 2-(3-thienyl)ethanol (1.3 eq.). The solution is chilled at 0° C. and DIAD [diisopropylazodicarboxylate] (21.65 g, 107.1 mmol, 1.5 eq.) is added dropwise. Then the reaction mixture is stirred at room temperature for 20 h and concentrated in vacuo. 3-Isopropoxy-5-(2-thiophene-3-yl-ethoxy)-benzoic acid methyl ester is obtained after column chromatography (cyclohexane/ethyl acetate) as yellow oil in a yield of 41%.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fcd0c090928947e79f4f3f5fde0441c4
Source dataset
uspto-grants-2012_08
Patent number
US08236824B2

Reaction notes

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